EP1215270B1 - Nematische Flüssigkristallmischung und diese enthaltende Anzeigen - Google Patents
Nematische Flüssigkristallmischung und diese enthaltende Anzeigen Download PDFInfo
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- EP1215270B1 EP1215270B1 EP01127805A EP01127805A EP1215270B1 EP 1215270 B1 EP1215270 B1 EP 1215270B1 EP 01127805 A EP01127805 A EP 01127805A EP 01127805 A EP01127805 A EP 01127805A EP 1215270 B1 EP1215270 B1 EP 1215270B1
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- liquid
- compounds
- crystal mixture
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- 0 CC=CCCC(CC1)CCC1C(CC1)CCC1*=C Chemical compound CC=CCCC(CC1)CCC1C(CC1)CCC1*=C 0.000 description 19
- RZXMPPFPUUCRFN-UHFFFAOYSA-N Cc(cc1)ccc1N Chemical compound Cc(cc1)ccc1N RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3048—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/16—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon double bonds, e.g. stilbenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0459—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF=CF- chain, e.g. 1,2-difluoroethen-1,2-diyl
Definitions
- the invention relates to new liquid crystal mixtures, their use in liquid crystal displays, in particular in twisted and highly twisted nematic liquid crystal displays (English: T wisted N ematic, short: TN; or S uper t wisted N ematic, short: STN) with very short switching times and good steepness and angle dependencies, and liquid crystal displays containing the new mixtures.
- TN displays are known, e.g. from M. Schadt and W. Helfrich, Appl. Phys. Lett., 18, 127 (1971).
- STN displays are known, e.g. out EP 0 131 216 B1; DE 34 23 993 A1; EP 0 098 070 A2; M. Schadt and F. Leenhouts, 17th Freiburg Liquid Crystal Working Conference (April 8-10, 1987); K. Kawasaki et al., SID 87 Digest 391 (20.6); M. Schadt and F. Leenhouts, SID 87 Digest 372 (20.1); K. Katoh et al., Japanese Journal of Applied Physics, Vol. 26, No.
- STN includes each higher here twisted display element with a twist angle according to the amount between 160 ° and 360 °, such as the display elements according to Waters et al. (C.M. Waters et al., Proc. Soc. Inf. Disp. (New York) (1985) (3rd Intern. Display Conference, Kobe, Japan), the STN-LCD's (DE OS 35 03 259), SBE-LCD's (T.J. Scheffer and J. Nehring, Appl. Phys. Lett. 45 (1984) 1021), OMI-LCD's (M. Schadt and F. Leenhouts, Appl. Phys. Lett. 50 (1987), 236, DST-LCD's (EP OS 0 246 842) or BW-STN-LCD's (K. Kawasaki et al., SID 87 Digest 391 (20.6)).
- STN ads stand out compared to standard TN ads much better slopes of the electro-optical characteristic and, at medium and higher multiplex rates, for example 32 to 64 and higher, through better contrast values.
- the contrast is higher and better due to the better dark value the angle dependence of the contrast is less than in STN displays with low multiplexing rates of, for example, less than 32.
- TN and STN advertisements with very short advertisements are of particular interest Switching times, especially at lower temperatures.
- the switching viscosities of the Liquid crystal mixtures optimized using mostly monotropic additives with relatively high vapor pressure. The achieved However, switching times were not sufficient for every application.
- the liquid crystal mixtures should have relatively large values for the ratio of the elastic constants K 33 / K 11 , as well as relatively small values for ⁇ / ⁇ ⁇ , where ⁇ is the dielectric anisotropy and ⁇ ⁇ the dielectric constant is perpendicular to the longitudinal axis of the molecule.
- the invention has for its object to liquid crystal mixtures Use in liquid crystal displays, especially in TN and STN displays to provide the disadvantages indicated above not or only to a lesser extent and at the same time short switching times, especially at low temperatures, and very good slopes as well as improved Temperature dependence of the operating voltage due to an improved Show frequency dependence of the dielectric constant.
- the compounds of formula I in particular increase birefringence of TN and STN mixtures while reducing the Threshold voltage without significantly increasing the clearing point affect.
- JP-A-10-245557, JP-A-09-208958, JP-A-08-176547, US-A-5 380 461, JP-A-05-070382 and DE-A-42 05 970 describe liquid crystal mixtures, which contain difluorstilbene or difluoroethenylene compounds, disclose however, no liquid crystal mixtures according to claim 1 of the present Registration.
- the invention also relates to corresponding liquid crystal mixtures for use in liquid crystal displays, especially in TN and STN displays, particularly preferred in medium and low multiplexed STN displays.
- R 5 is alkyl or alkoxy having 1 to 8 C atoms or straight-chain 1 E or 3 E alkenyl having 2 to 7 C atoms.
- R 6 is -QY and those in which R 5 and R 6 are -QY.
- QY is preferably F, Cl, OCF 3 or OCF 2 H, in particular F or OCF 3 .
- Particularly preferred compounds of the formula I are selected from the following formulas wherein alkyl is an alkyl group having 1 to 8 carbon atoms and QY has the meaning of formula I, and in particular F or OCF 3 .
- Particularly preferred compounds of the formula II are selected from the formulas IIa to IIg wherein R 3a and R 4a each independently represent H, CH 3 , C 2 H 5 or nC 3 H 7 and alkyl is an alkyl group having 1 to 8 carbon atoms.
- Particularly preferred compounds of the formula II * are those in which L 1 and / or L 2 F and QY F or OCF 3 .
- R 3 denotes 1E-alkenyl or 3E-alkenyl having 2 to 7, in particular 2, 3 or 4, carbon atoms.
- R 3a is H, CH 3 , C 2 H 5 or nC 3 H 7 , in particular H or CH 3 .
- the polar compounds of the formula II * with a dielectric anisotropy of more than + 1.5 can be assigned to component A defined above.
- R particularly preferably denotes alkyl or alkoxy with 1 to 8 carbon atoms or alkenyl with 2 to 7 carbon atoms.
- Mixtures which contain one or more compounds of the formula IIIb and / or IIIc, in which R denotes alkenyl having 2 to 7 C atoms and L 1 and L 2 H or F, preferably both H, are very particularly preferred.
- R 3a is H, CH 3 , C 2 H 5 or nC 3 H 7 , in formula IIIb-1 and IIIb-2 preferably H or CH 3 , in formula IIIc-1 and IIIc-2 preferably H or C 2 H 5 , means.
- Mixtures which contain one or more compounds of the formula IIIh, in which L 2 is H and L 1 is H or F, in particular F, are furthermore preferred.
- component A preferably contains one or more 3,4,5-trifluorophenyl compounds of the following formulas and optionally one or more compounds with a polar end group of the following formulas wherein R has one of the meanings given above and L 3 and L 4 each independently represent H or F.
- R particularly preferably denotes alkyl or alkoxy having 1 to 8 carbon atoms.
- Preferred liquid crystal mixtures preferably contain one or more compounds of component A in a proportion of 15% to 80%, particularly preferably 20% to 70%. These compounds have a dielectric anisotropy ⁇ ⁇ +3, in particular ⁇ ⁇ +8, particularly preferably ⁇ ⁇ +12.
- Preferred liquid crystal mixtures contain one or more compounds of component B, preferably in a proportion of 20 to 85%, particularly preferably in a proportion of 30 to 75%.
- the compounds of group B are distinguished in particular by their low values for the rotational viscosity ⁇ 1 .
- the 1,4-phenylene groups in IV10 to IV19 and IV23 to IV 32 can each independently of one another also by fluorine one or more times be substituted.
- R 1 and R 2 in the compounds of the formulas IV1 to IV30 particularly preferably denote straight-chain alkyl or alkoxy having 1 to 12 carbon atoms.
- the liquid-crystalline mixtures optionally contain an optically active component C in an amount such that the ratio between the layer thickness (distance between the carrier plates) and the natural pitch of the chiral nematic liquid-crystal mixture is greater than 0.2.
- an optically active component C in an amount such that the ratio between the layer thickness (distance between the carrier plates) and the natural pitch of the chiral nematic liquid-crystal mixture is greater than 0.2.
- the skilled person has a large number of, in some cases commercially available, chiral dopants available for the component, for example cholesteryl nonanoate, S-811 from Merck KGaA, Darmstadt and CB15 (BDH, Poole, UK). The choice of dopants is not critical in itself.
- the proportion of the compounds of component C is preferably 0 up to 10%, in particular 0 to 5%, particularly preferably 0 to 3%.
- Particularly preferred compounds of the formula Te are those in which one, two or three of the radicals L 1 to L 6 are F and the other are H, L 1 and L 2 or L 3 and L 4 or L 5 and L 6 not both mean F at the same time.
- the proportion of the compounds from the group containing Ta and Tb is preferably 5 to 50%, in particular 10 to 40%.
- the share of Compounds of the formula Th is preferably 2 to 35%, in particular 4 up to 25%.
- the proportion of the compounds of the formulas Ta to Th is preferably 2 to 55%, especially 5 to 35%.
- the mixtures according to the invention can also optionally contain up to 20% of one or more compounds with a dielectric anisotropy of less than -2 ( component D) .
- the mixtures contain compounds of component D , these are preferably one or more compounds having the structural element 2,3-difluoro-1,4-phenylene, for example compounds according to DE-OS 38 07 801, 38 07 861, 38 07 863, 38 07 864 or 38 07 908.
- compounds according to the international patent application PCT / DE 88/00133 are particularly preferred.
- component D is, for example, derivatives of 2,3-dicyanohydroquinones or cyclohexane derivatives with the structural element or according to DE-OS 32 31 707 or DE-OS 34 07 013.
- the liquid crystal displays according to the invention preferably contain no compounds of component D.
- alkenyl in the meaning of R, R 1 , R 2 , R 3 and R 4 includes straight-chain and branched alkenyl groups, in the case of R, R 1 and R 2 2-12, in the case of R 3 and R 4 with 2-7 carbon atoms, especially the straight-chain groups.
- alkenyl groups are C 2 -C 7 -1E-alkenyl, C 4 -C 7 -3E-alkenyl, C 5 -C 7 -4-alkenyl, C 6 -C 7 -5-alkenyl, and C 7 -6- Alkenyl, especially C 2 -C 7 -1E-alkenyl, C 4 -C 7 -3E-alkenyl and C 5 -C 7 -4-alkenyl.
- alkenyl groups are vinyl, 1E-propenyl, 1E-butenyl, 1E-pentenyl, 1E-hexenyl, 1E-heptenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 3E-heptenyl, 4-pentenyl, 4Z-hexenyl, 4E-hexenyl, 4Z-heptenyl, 5-hexenyl, 6-heptenyl and the like. Groups of up to 5 Carbon atoms are generally preferred.
- Liquid crystal mixtures are dielectrically positive with ⁇ ⁇ 1.
- Special preferred are liquid crystal mixtures with ⁇ ⁇ 3, in particular with ⁇ ⁇ 5.
- the liquid crystal mixtures according to the invention have favorable values for the threshold voltage V 10/0/20 and for the rotational viscosity ⁇ 1 . If the value for the optical path difference d ⁇ ⁇ n is specified, the value for the layer thickness d is determined by the optical anisotropy ⁇ n. In particular, in the case of relatively high values for d ⁇ ⁇ n, the use of liquid crystal mixtures according to the invention with a relatively high value for the optical anisotropy is generally preferred, since the value for d can then be chosen to be relatively small, which leads to more favorable values for the switching times. However, such liquid crystal displays according to the invention which contain liquid crystal mixtures according to the invention with smaller values for ⁇ n are also characterized by advantageous values for the switching times.
- the liquid crystal mixtures according to the invention are further through marked advantageous values for the steepness of the electro-optical characteristic, and can be used especially at temperatures above 20 ° C high multiplex rates are operated.
- the Liquid crystal mixtures according to the invention have high stability and favorable values for the electrical resistance and the Frequency dependence of the threshold voltage.
- the invention Liquid crystal displays have a wide working temperature range and a good angle dependence of the contrast.
- the structure of the liquid crystal display elements according to the invention Polarizers, electrode base plates and electrodes with such Surface treatment that the preferred orientation (director) of each adjacent liquid crystal molecules from one to the other Electrode usually 160 ° to 720 ° against each other is twisted, corresponds to the usual for such display elements Construction.
- the concept of the usual design is broad and also includes all modifications and modifications of the TN and STN cells, especially matrix display elements as well as the additional one Display elements containing magnets.
- the surface tilt angle on the two carrier plates can be the same or to be different.
- the same tilt angles are preferred.
- Preferred TN ads indicate angles of attack between the longitudinal axis of the molecules the surface of the carrier plates and the carrier plates from 0 ° to 7 °, preferably 0.01 ° to 5 °, in particular 0.1 to 2 °.
- the angle of attack is 1 ° to 30 °, preferably 1 ° to 12 ° and especially at 3 ° to 10 °.
- the twist angle of the TN mixture in the cell is based on the amount between 22.5 ° and 170 °, preferably between 45 ° and 130 ° and especially between 80 ° and 115 °.
- the twist angle of the STN mixture in the cell from orientation layer to orientation layer the amount between 100 ° and 600 °, preferably between 170 ° and 300 ° and in particular between 180 ° and 270 °.
- liquid crystal mixtures which can be used according to the invention takes place in a conventional manner. Usually the one you want Quantity of components used in smaller quantities in the components that make up the main constituent are dissolved, expedient at elevated temperature. It is also possible to find solutions to the Components in an organic solvent, e.g. in acetone, Chloroform or methanol to mix and the solvent after To remove mixing again, for example by distillation.
- an organic solvent e.g. in acetone, Chloroform or methanol
- the liquid crystal mixtures according to the invention are also suitable for Use as liquid crystal (LC) media in cholesteric Liquid crystal (CFRP) displays, in particular SSCT (English “surface stabilized cholesteric texture ”) and PSCT (polymer stabilized) cholesteric texture ”) Displays, for example in WO 92/19695, US 5,384,067, US 5,453,863, US 6,172,720 or US 5,661,533.
- CFRP displays typically contain a cholesteric LC medium consisting of a nematic component and an optically active one Component, which is clearly in comparison to TN and STN displays has higher helical twist, and selective reflection from circular shows polarized light. The reflection wavelength corresponds to the product from the pitch of the cholesteric helix and the middle one Refractive index of the CFRP medium.
- the LC mixtures according to the invention are one or added several chiral dopants, their twisting power and Concentration are chosen so that the LC medium is cholesteric Phase at room temperature and a reflection wavelength has, preferably in the visible, UV or IR range of electromagnetic spectrum, in particular between 400 and 800 nm, lies.
- Suitable dopants are known to the person skilled in the art and are commercially available available, such as cholesteryl nonanoate (CN), CB15, R / S-811, R / S-1011, R / S-2011, R / S-3011 or R / S-4011 (Merck KGaA, Darmstadt).
- Highly twisting dopants with a chiral are particularly suitable Sugar residue, especially sorbitol derivatives as in WO 98/00428 described. If two or more dopants are added, can these same or opposite sense of rotation and same or have opposite temperature dependence of the twist.
- CFRP media containing a as a nematic component LC mixture according to the invention and an optically active component or more chiral dopants are another subject of present invention.
- the present invention relates to CFRP ads, especially SSCT and PSCT ads, containing CFRP media as described above.
- the compounds of formula I and their preparation are partly from the JP-A-03-41037 known.
- the new compounds of formula I are one further subject of the present application.
- the dielectrics can also be other known to those skilled in the art Literature contains additives described. For example, 0-15% pleochroic dyes are added.
- the TN and STN displays preferably contain liquid-crystalline mixtures which are composed of one or more compounds from Tables A and B.
- a TN and STN mixture consisting of PCH-3 13.00% Klp. 104.0 ° C K6 7:00 % .DELTA.n .1219 ME2N.F 3.00% ME3N.F 2.00% V 10 2.30 V ME4N.F 4.00% S 1,045 CBC 33 4.00% t ave 300 ms CBC-33F 4.00% CCP-V-1 14.00% CCP-V2-1 15.00% CPP 1V2-2 5.00% CCG-VF 9.00% CC-5-V 8:00 pm %
- a TN and STN mixture consisting of PCH-3 13.00% Klp. 102.0 ° C K6 7:00 % .DELTA.n .1358 ME2N.F 3.00% ⁇ 9.6 ME3N.F 2.00% V 10 2,19V ME4N.F 4.00% S 1,032 CBC 33 4.00% t ave 319 ms CBC-33F 4.00% CCP-V-1 14.00% CCP-V2-1 15.00% CPP 1V2-2 5.00% CCG-VF 9.00% IS-7134 8:00 pm % has a higher birefringence ⁇ n and a reduced threshold voltage V 10 and improved slope S compared to comparative example 1.
- a TN and STN mixture consisting of PCH-3 13.00% Klp. 106.0 ° C K6 7:00 % .DELTA.n .1636 ME2N.F 3.00% ⁇ 10.7 ME3N.F 2.00% V 10 2,08V ME4N.F 4.00% S 1.066 CBC 33 4.00% t ave 153 ms CBC-33F 4.00% CCP-V-1 14.00% CCP-V2-1 15.00% CPP 1V2-2 5.00% CCG-VF 9.00% IS-7135 8:00 pm % has a higher birefringence ⁇ n and a reduced threshold voltage V 10 compared to Comparative Example 1.
- a TN and STN mixture consisting of PCH-3 13.00% Klp. 110.5 ° C K6 7:00 % .DELTA.n .1680 ME2N.F 3.00% ⁇ 9.9 ME3N.F 2.00% V 10 2.01 V ME4N.F 4.00% S 1,112 CBC 33 4.00% t ave 135 ms CBC-33F 4.00% CCP-V-1 14.00% CCP-V2-1 15.00% CPP 1V2-2 5.00% CCG-VF 9.00% IS-7151 8:00 pm % has a higher birefringence ⁇ n and a reduced threshold voltage V 10 compared to Comparative Example 1.
- a TN and STN mixture consisting of PCH-3 13.00% Klp. 102.0 ° C K6 7:00 % .DELTA.n .1618 ME2N.F 3.00% ⁇ 11.3 ME3N.F 2.00% V 10 1.89 V ME4N.F 4.00% S 1,074 CBC 33 4.00% t ave 172 ms CBC-33F 4.00% CCP-V-1 14.00% CCP-V2-1 15.00% CPP 1V2-2 5.00% CCG-VF 9.00% IS-7157 8:00 pm % has a higher birefringence ⁇ n and a reduced threshold voltage V 10 compared to Comparative Example 1.
- a TN and STN mixture consisting of PCH-3 13.00% Klp. 99.5 ° C K6 7:00 % .DELTA.n .1374 ME2N.F 3.00% ⁇ 9.1 ME3N.F 2.00% V 10 2.16 V ME4N.F 4.00% S 1,044 CBC 33 4.00% t ave 315 ms CBC-33F 4.00% CCP-V-1 14.00% CCP-V2-1 15.00% CPP 1V2-2 5.00% CCG-VF 9.00% IS-7197 8:00 pm % has a higher birefringence ⁇ n and a reduced threshold voltage V 10 compared to Comparative Example 1.
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- Crystallography & Structural Chemistry (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
- A1
- trans-1,4-Cyclohexylen, 1,4-Phenylen, 3-Fluor-1,4-phenylen oder 3,5-Difluor-1,4-phenylen,
- A2 und A3
- jeweils unabhängig voneinander eine der Bedeutungen von A1 oder eine Einfachbindung,
- A4
- 1,4-Phenylen oder trans-1,4-Cyclohexylen,
- Z1
- -CF=CF-, -CR0=CF- oder -CF=CR0-,
- Z2 und Z3
- jeweils unabhängig voneinander -O-, -COO-, -OCO-, -CH2O-, -OCH2-, -CH2CH2-, -CF2O-, -OCF2-, -CF2CF2-, -CH=CH-, -C≡C-, eine Einfachbindung oder eine der Bedeutungen von Z1,
- R0
- H oder CH3,
- R3
- eine Alkenylgruppe mit 2 bis 7 C-Atomen,
- R4
- eine Alkyl-, Alkoxy- oder Alkenylgruppe mit 1 bis 12 C-Atomen, wobei auch ein oder zwei nicht benachbarte CH2-Gruppen durch -O-, -CH=CH-, -CO-, -OCO- oder -COO- so ersetzt sein können, daß O-Atome nicht direkt miteinander verknüpft sind,
- R5 und R6
- jeweils unabhängig voneinander Alkyl, Alkoxy oder Alkenyl mit 1 bis 12 C-Atomen, wobei auch ein oder zwei nicht benachbarte CH2- Gruppen durch -O-, -CH=CH-, -CO-, -OCO- oder -COO- so ersetzt sein können, daß O-Atome nicht direkt miteinander verknüpft sind, CN oder -Q-Y,
- Q
- CF2, OCF2, CFH, OCFH oder eine Einfachbindung,
- Y
- F oder Cl,
- L1, L2 und L3
- jeweils unabhängig voneinander H oder F, und
- a
- 0 oder 1
- sie besitzen eine niedrige Viskosität,
- sie besitzen eine niedrige Schwellenspannung und Betriebsspannung,
- sie bewirken lange Lagerzeiten in der FK-Anzeige bei tiefen Temperaturen.
- A1
- trans-1,4-Cyclohexylen, 1,4-Phenylen, 3-Fluor-1,4-phenylen oder 3,5-Difluor-1,4-phenylen,
- A2 und A3
- jeweils unabhängig voneinander eine der Bedeutungen von A1 oder eine Einfachbindung,
- A4
- 1,4-Phenylen oder trans-1,4-Cyclohexylen,
- Z1
- -CF=CF-, -CR0=CF- oder -CF=CR0-,
- Z2 und Z3
- jeweils unabhängig voneinander -O-, -COO-, -OCO-, -CH2O-, -OCH2-, -CH2CH2-, -CF2O-, -OCF2-, -CF2CF2-, -CH=CH-, -C≡C-, eine Einfachbindung oder eine der Bedeutungen von Z1,
- R0
- H oder CH3,
- R3
- eine Alkenylgruppe mit 2 bis 7 C-Atomen,
- R4
- eine Alkyl, Alkoxy- oder Alkenylgruppe mit 1 bis 12 C-Atomen, wobei auch ein oder zwei nicht benachbarte CH2-Gruppen durch -O-, -CH=CH-, -CO-, -OCO- oder -COO- so ersetzt sein können, daß O-Atome nicht direkt miteinander verknüpft sind,
- R5 und R6
- jeweils unabhängig voneinander Alkyl, Alkoxy oder Alkenyl mit 1 bis 12 C-Atomen, wobei auch ein oder zwei nicht benachbarte CH2- Gruppen durch -O-, -CH=CH-, -CO-, -OCO- oder -COO- so ersetzt sein können, daß O-Atome nicht direkt miteinander verknüpft sind, CN oder -Q-Y,
- Q
- CF2, OCF2, CFH, OCFH oder eine Einfachbindung,
- Y
- F oder Cl,
- L1, L2 und L3
- jeweils unabhängig voneinander H oder F, und
- a
- 0 oder 1
- zwei Trägerplatten, die mit einer Umrandung eine Zelle bilden,
- einer in der Zelle befindlichen nematischen Flüssigkristallmischung mit positiver dielektrischer Anisotropie,
- Elektrodenschichten mit Orientierungsschichten auf den Innenseiten der Trägerplatten,
- einem Anstellwinkel zwischen der Längsachse der Moleküle an der Oberfläche der Trägerplatten und den Trägerplatten von 0 Grad bis 30 Grad, und
- einem Verdrillungswinkel der Flüssigkristallmischung in der Zelle von Orientierungsschicht zu Orientierungsschicht dem Betrag nach zwischen 22,5° und 600°,
- einer nematischen Flüssigkristallmischung bestehend aus
- a) 15 - 80 Gew.% einer flüssigkristallinen Komponente A, bestehend aus einer oder mehreren Verbindungen mit einer dielektrischen Anisotropie von über +1,5;
- b) 20 - 85 Gew.% einer flüssigkristallinen Komponente B, bestehend aus einer oder mehreren Verbindungen mit einer dielektrischen Anisotropie zwischen -1,5 und +1,5;
- c) 0 - 20 Gew.% einer flüssigkristallinen Komponente D, bestehend aus einer oder mehreren Verbindungen mit einer dielektrischen Anisotropie von unter -1,5 und
- d) gegebenenfalls einer optisch aktiven Komponente C in einer Menge, daß das Verhältnis zwischen Schichtdicke (Abstand der Trägerplatten) und natürlicher Ganghöhe der chiralen nematischen Flüssigkristallmischung etwa 0,2 bis 1,3 beträgt,
- A4
- 1,4-Phenylen oder trans-1,4-Cyclohexylen,
- R3
- eine Alkenylgruppe mit 2 bis 7 C-Atomen,
- R4
- eine Alkyl-, Alkoxy- oder Alkenylgruppe mit 1 bis 12 C-Atomen, wobei auch ein oder zwei nicht benachbarte CH2-Gruppen durch -O-, -CH=CH-, -CO-, -OCO- oder -COO- so ersetzt sein können, daß O-Atome nicht direkt miteinander verknüpft sind, und
- a
- 0 oder 1
- R3
- eine Alkenylgruppe mit 2 bis 7 C-Atomen,
- Q
- CF2, OCF2, CFH, OCFH oder eine Einfachbindung,
- Y
- F oder Cl, und
- L1 und L2
- jeweils unabhängig voneinander H oder F
- R
- eine Alkyl-, Alkoxy- oder Alkenylgruppe mit 1 bis 12 C-Atomen, wobei auch ein oder zwei nicht benachbarte CH2-Gruppen durch -O-, -CH=CH-, -CO-, -OCO- oder -COO- so ersetzt sein können, daß O-Atome nicht direkt miteinander verknüpft sind, und
- L1, L2 und L3
- jeweils unabhängig voneinander H oder F bedeuten.
- R1 und R2
- jeweils unabhängig voneinander eine Alkyl-, Alkoxy- oder Alkenylgruppe mit 1 bis 12 C-Atomen, wobei auch ein oder zwei nicht benachbarte CH2-Gruppen durch -O-, -CH=CH-, -CO-, -OCO- oder -COO- so ersetzt sein können, daß O-Atome nicht direkt miteinander verknüpft sind, und
- L
- H oder F
- Z4
- -CO-O-, -CH2CH2- oder eine Einfachbindung, und
- L1 bis L6
- jeweils unabhängig voneinander H oder F bedeuten.
- eine oder mehrere Verbindungen ausgewählt aus den Formeln Ib, Ic, Id, If und Ig,
- eine, zwei oder drei Verbindungen der Formel I,
- 3 bis 40 %, insbesondere 8 bis 35 %, besonders bevorzugt 15 bis 25 % einer oder mehrerer Verbindungen der Formel I,
- 5 bis 60 %, insbesondere 15 bis 50 % einer oder mehrerer Alkenylverbindungen der Formel II und II*,
- eine oder mehrere Alkenylverbindungen ausgewählt aus den Formeln IIf, IIg, IIh, IIi und II*a, worin alkyl eine Alkylgruppe mit 1 bis 8 C-Atomen und R3a H oder CH3 bedeutet,
- eine oder mehrere, insbesondere zwei bis fünf Verbindungen der Formel IIIa, IIIb, IIIc und/oder IIIh,
- eine oder mehrere Verbindungen der Formel IV25 und/oder IV27, wobei L in Formel IV 25 H oder F, besonders bevorzugt F bedeutet. Der Anteil dieser Verbindungen in den Flüssigkristallmischungen liegt vorzugsweise bei 10 bis 45 %, insbesondere bei 15 bis 40 %,
- mehr als 20 % an Verbindungen mit positiver dielektrischer Anisotropie, insbesondere mit Δε ≥ +12,
Code für R1, R2, L1, L2, L3 | R1 | R2 | L1 | L2 | L3 |
nm | CnH2n+1 | CmH2m+1 | H | H | H |
nOm | OCnH2n+1 | CmH2m+1 | H | H | H |
nO.m | CnH2n+1 | OCmH2m+1 | H | H | H |
n | CnH2n+1 | CN | H | H | H |
nN.F | CnH2n+1 | CN | H | H | F |
nN.F.F | CnH2n+1 | CN | H | F | F |
nF | CnH2n+1 | F | H | H | H |
nOF | OCnH2n+1 | F | H | H | H |
nF.F | CnH2n+1 | F | H | H | F |
nmF | CnH2n+1 | CmH2m+1 | F | H | H |
nOCF3 | CnH2n+1 | OCF3 | H | H | H |
n-Vm | CnH2n+1 | -CH=CH-CmH2m+1 | H | H | H |
nV-Vm | CnH2n+1-CH=CH- | -CH=CH-CmH2m+1 | H | H | H |
- Klp.
- Klärpunkt (Phasenübergangs-Temperatur nematisch-isotrop),
- S-N
- Phasenübergangs-Temperatur smektisch-nematisch,
- Visk.
- Fließviskosität (soweit nicht anders angegeben bei 20 °C),
- Δn
- optische Anisotropie (589 nm, 20 °C)
- no
- ordentlicher Brechungsindex (589 nm, 20 °C)
- Δε
- dielektrische Anisotropie (1 kHz, 20 °C)
- ε⊥
- Dielektrizitätskonstante senkrecht zur Moleküllängsachse (1 kHz, 20 °C)
- γ1
- Rotationsviskosität
- S
- Kennliniensteilheit = V90/V10
- V10
- Schwellenspannung = charakteristische Spannung bei einem relativen Kontrast von 10 %,
- V90
- charakteristische Spannung bei einem relativen Kontrast von 90 %,
- tave
- ton + toff / 2 (mittlere Schaltzeit)
- ton
- Zeit vom Einschalten bis zur Erreichung von 90 % des maximalen Kontrastes,
- toff
- Zeit vom Ausschalten bis zur Erreichung von 10 % des maximalen Kontrastes,
- Mux
- Multiplexrate
- tstore
- Tieftemperatur-Lagerstabilität in Stunden (- 20 °C, - 30 °C, - 40 °C)
PCH-3 | 13.00 % | Klp. | 104,0 °C |
K6 | 7.00 % | Δn | 0,1219 |
ME2N.F | 3.00 % | ||
ME3N.F | 2.00 % | V10 | 2,30 V |
ME4N.F | 4.00 % | S | 1,045 |
CBC-33 | 4.00 % | tave | 300 ms |
CBC-33F | 4.00 % | ||
CCP-V-1 | 14.00 % | ||
CCP-V2-1 | 15.00 % | ||
CPP-1V2-2 | 5.00 % | ||
CCG-V-F | 9.00 % | ||
CC-5-V | 20.00 % |
PCH-3 | 13.00 % | Klp. | 102,0°C |
K6 | 7.00 % | Δn | 0,1358 |
ME2N.F | 3.00 % | Δε | 9.6 |
ME3N.F | 2.00 % | V10 | 2,19V |
ME4N.F | 4.00 % | S | 1,032 |
CBC-33 | 4.00 % | tave | 319 ms |
CBC-33F | 4.00 % | ||
CCP-V-1 | 14.00 % | ||
CCP-V2-1 | 15.00 % | ||
CPP-1V2-2 | 5.00 % | ||
CCG-V-F | 9.00 % | ||
IS-7134 | 20.00 % |
PCH-3 | 13.00 % | Klp. | 106,0 °C |
K6 | 7.00 % | Δn | 0,1636 |
ME2N.F | 3.00 % | Δε | 10,7 |
ME3N.F | 2.00 % | V10 | 2,08V |
ME4N.F | 4.00 % | S | 1,066 |
CBC-33 | 4.00 % | tave | 153 ms |
CBC-33F | 4.00 % | ||
CCP-V-1 | 14.00 % | ||
CCP-V2-1 | 15.00 % | ||
CPP-1V2-2 | 5.00 % | ||
CCG-V-F | 9.00 % | ||
IS-7135 | 20.00 % |
PCH-3 | 13.00 % | Klp. | 110,5 °C |
K6 | 7.00 % | Δn | 0,1680 |
ME2N.F | 3.00 % | Δε | 9,9 |
ME3N.F | 2.00 % | V10 | 2,01 V |
ME4N.F | 4.00 % | S | 1,112 |
CBC-33 | 4.00 % | tave | 135 ms |
CBC-33F | 4.00 % | ||
CCP-V-1 | 14.00 % | ||
CCP-V2-1 | 15.00 % | ||
CPP-1V2-2 | 5.00 % | ||
CCG-V-F | 9.00 % | ||
IS-7151 | 20.00 % |
PCH-3 | 13.00 % | Klp. | 102,0 °C |
K6 | 7.00 % | Δn | 0,1618 |
ME2N.F | 3.00 % | Δε | 11,3 |
ME3N.F | 2.00 % | V10 | 1,89 V |
ME4N.F | 4.00 % | S | 1,074 |
CBC-33 | 4.00 % | tave | 172 ms |
CBC-33F | 4.00 % | ||
CCP-V-1 | 14.00 % | ||
CCP-V2-1 | 15.00 % | ||
CPP-1V2-2 | 5.00 % | ||
CCG-V-F | 9.00 % | ||
IS-7157 | 20.00 % |
PCH-3 | 13.00 % | Klp. | 99,5 °C |
K6 | 7.00 % | Δn | 0,1374 |
ME2N.F | 3.00 % | Δε | 9,1 |
ME3N.F | 2.00 % | V10 | 2,16 V |
ME4N.F | 4.00 % | S | 1,044 |
CBC-33 | 4.00 % | tave | 315 ms |
CBC-33F | 4.00 % | ||
CCP-V-1 | 14.00 % | ||
CCP-V2-1 | 15.00 % | ||
CPP-1V2-2 | 5.00 % | ||
CCG-V-F | 9.00 % | ||
IS-7197 | 20.00 % |
Claims (9)
- Flüssigkristallmischung, dadurch gekennzeichnet, daß sie mindestens eine Verbindung der Formel I enthält und mindestens eine Verbindung der Formel II und/oder II* enthält worin
- A1
- trans-1,4-Cyclohexylen, 1,4-Phenylen, 3-Fluor-1,4-phenylen oder 3,5-Difluor-1,4-phenylen,
- A2 und A3
- jeweils unabhängig voneinander eine der Bedeutungen von A1 oder eine Einfachbindung,
- A4
- 1,4-phenylen oder trans-1,4-Cyclohexylen,
- Z1
- -CF=CF-, -CR0=CF- oder -CF=CR0-,
- Z2 und Z3
- jeweils unabhängig voneinander -O-, -COO-, -OCO-, -CH2O-, -OCH2-, -CH2CH2-, -CF2O-, -OCF2-, -CF2CF2-, -CH=CH-, -C≡C-, eine Einfachbindung oder eine der Bedeutungen von Z1,
- R0
- H oder CH3,
- R3
- eine Alkenylgruppe mit 2 bis 7 C-Atomen,
- R4
- eine Alkyl-, Alkoxy- oder Alkenylgruppe mit 1 bis 12 C-Atomen, wobei auch ein oder zwei nicht benachbarte CH2- Gruppen durch -O-, -CH=CH-, -CO-, -OCO- oder -COO- so ersetzt sein können, daß O-Atome nicht direkt miteinander verknüpft sind,
- R5 und R6
- jeweils unabhängig voneinander Alkyl, Alkoxy oder Alkenyl mit 1 bis 12 C-Atomen, wobei auch ein oder zwei nicht benachbarte CH2-Gruppen durch -O-, -CH=CH-, -CO-, -OCO- oder -COO- so ersetzt sein können, daß O-Atome nicht direkt miteinander verknüpft sind, CN oder -Q-Y,
- Q
- CF2, OCF2, CFH, OCFH oder eine Einfachbindung,
- Y
- F oder Cl,
- L1, L2 und L3
- jeweils unabhängig voneinander H oder F, und
- a
- 0 oder 1
- Flüssigkristallmischung nach Anspruch 1, dadurch gekennzeichnet, daß sie eine oder mehrere Verbindungen der folgenden Formeln enthält worin
- R
- eine Alkyl-, Alkoxy- oder Alkenylgruppe mit 1 bis 12 C-Atomen, wobei auch ein oder zwei nicht benachbarte CH2- Gruppen durch -O-, -CH=CH-, -CO-, -OCO- oder -COO- so ersetzt sein können, daß O-Atome nicht direkt miteinander verknüpft sind, und
- L1 bis L3
- jeweils unabhängig voneinander H oder F
- Flüssigkristallmischung nach einem der Ansprüche 1 und 2, dadurch gekennzeichnet, daß sie eine oder mehrere Verbindungen der folgenden Formeln enthält worin
- R1 und R2
- jeweils unabhängig voneinander eine Alkyl-, Alkoxy- oder Alkenylgruppe mit 1 bis 12 C-Atomen, wobei auch ein oder zwei nicht benachbarte CH2-Gruppen durch -O-, -CH=CH-, -CO-, -OCO- oder -COO- so ersetzt sein können, daß O-Atome nicht direkt miteinander verknüpft sind, und
- L
- H oder F
- Flüssigkristallmischung nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß sie 3 bis 40 % einer oder mehrerer Verbindungen der Formel I enthält.
- Flüssigkristallanzeige enthaltend eine Flüssigkristallmischung nach einem der Ansprüche 1 bis 6.
- TN- oder STN-Flüssigkristallanzeige mitzwei Trägerplatten, die mit einer Umrandung eine Zelle bilden,einer in der Zelle befindlichen nematischen Flüssigkristallmischung mit positiver dielektrischer Anisotropie,Elektrodenschichten mit Orientierungsschichten auf den Innenseiten der Trägerplatten,einem Anstellwinkel zwischen der Längsachse der Moleküle an der Oberfläche der Trägerplatten und den Trägerplatten von 0 Grad bis 30 Grad, undeinem Verdrillungswinkel der Flüssigkristallmischung in der Zelle von Orientierungsschicht zu Orientierungsschicht dem Betrag nach zwischen 22,5° und 600°,einer nematischen Flüssigkristallmischung bestehend ausa) 15 - 80 Gew.% einer flüssigkristallinen Komponente A, bestehend aus einer oder mehreren Verbindungen mit einer dielektrischen Anisotropie von über +1,5;b) 20 - 85 Gew.% einer flüssigkristallinen Komponente B, bestehend aus einer oder mehreren Verbindungen mit einer dielektrischen Anisotropie zwischen -1,5 und +1,5;c) 0 - 20 Gew.% einer flüssigkristallinen Komponente D, bestehend aus einer oder mehreren Verbindungen mit einer dielektrischen Anisotropie von unter -1,5 undd) gegebenenfalls einer optisch aktiven Komponente C in einer Menge, daß das Verhältnis zwischen Schichtdicke (Abstand der Trägerplatten) und natürlicher Ganghöhe der chiralen nematischen Flüssigkristallmischung etwa 0,2 bis 1,3 beträgt,
- Cholesterische Flüssigkristallanzeige, SSCT- oder PSCT-Anzeige, enthaltend als optisch aktive Komponente einen oder mehrere chirale Dotierstoffe und als nematische Komponente eine Flüssigkristallmischung nach einem der Ansprüche 1 bis 6.
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DE10062986A DE10062986A1 (de) | 2000-12-16 | 2000-12-16 | TN- und STN-Flüssigkristallanzeigen |
DE10062986 | 2000-12-16 |
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EP1215270B1 true EP1215270B1 (de) | 2004-09-01 |
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EP (1) | EP1215270B1 (de) |
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DE50307284D1 (de) * | 2002-10-15 | 2007-06-28 | Merck Patent Gmbh | Flüssigkristalline Verbindungen mit CHFO-Brücke |
WO2006133783A1 (de) | 2005-06-13 | 2006-12-21 | Merck Patent Gmbh | Flüssigkristallines medium und flüssigkristallanzeige mit 1,2-difluorethenverbindungen |
EP1764405A1 (de) * | 2005-09-20 | 2007-03-21 | Rolic AG | Funktionalisierte photoreaktive Verbindungen |
EP2031040B1 (de) * | 2007-08-30 | 2011-10-26 | Merck Patent GmbH | Flüssigkristallines Medium |
DE102011008687A1 (de) | 2010-02-11 | 2011-08-11 | Merck Patent GmbH, 64293 | Flüssigkristallanzeige und Flüssigkristallines Medium |
JP5663957B2 (ja) * | 2010-05-28 | 2015-02-04 | Jnc株式会社 | 誘電率異方性が負のトランスモノフルオロエチレン液晶性化合物、これを用いた液晶組成物および液晶表示素子 |
CN103710030B (zh) * | 2013-11-27 | 2016-01-20 | 合肥工业大学 | 一种氰基取代二苯乙烯型液晶材料及其制备工艺及应用 |
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US5380461A (en) * | 1990-04-13 | 1995-01-10 | Seimi Chemical Co., Ltd. | Trans-dihalogenostilbene compounds and liquid crystal electro-optical devices using them |
JPH0570382A (ja) * | 1991-09-11 | 1993-03-23 | Asahi Glass Co Ltd | トランス−モノフルオロエチレン誘導体化合物及びそれを含有する液晶組成物 |
DE4205970C2 (de) * | 1992-02-13 | 2002-08-14 | Merck Patent Gmbh | Fluorvinylenverbindungen und flüssigkristallines Medium |
JPH08176547A (ja) * | 1994-12-21 | 1996-07-09 | Asahi Glass Co Ltd | 液晶組成物及びそれを用いた液晶表示装置 |
JPH09208958A (ja) * | 1996-01-31 | 1997-08-12 | Seimi Chem Co Ltd | 液晶組成物および液晶表示素子 |
JPH10245557A (ja) * | 1997-03-03 | 1998-09-14 | Seimi Chem Co Ltd | 液晶組成物および液晶表示素子 |
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ATE275182T1 (de) | 2004-09-15 |
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